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Substance Name: Cephalothin
RN: 153-61-7
UNII: R72LW146E6
InChIKey: XIURVHNZVLADCM-IUODEOHRSA-N

Note

  • A cephalosporin antibiotic.

Molecular Formula

  • C16-H16-N2-O6-S2

Molecular Weight

  • 396.4424
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibiotics
  • Drug / Therapeutic Agent
  • Mutation Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Cefalotin [INN]
  • Cephalothin

MeSH Heading

  • Cephalothin

Synonyms

  • 3-(Acetoxymethyl)-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
  • 3-(Hydroxymethyl)-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid acetate
  • 3-Acetoxymethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid
  • 6R-trans-3-((Acetyloxy)methyl)-8-oxo-7-((2-thienylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)-oct-2-ene-2-carboxylic acid
  • 7-(2-(2-Thienyl)acetylamido)cephalosporanic acid
  • 7-(2-Thienylacetamido)cephalosporanic acid
  • 7-(Thiophene-2-acetamido)cephalosporanic acid
  • 7-(Thiophene-2-acetamido)cephalosporin
  • Averon-1
  • BRN 0945586
  • Cefalothin
  • Cefalotin
  • Cefalotina
  • Cefalotina [INN-Spanish]
  • Cefalotine
  • Cefalotine [INN-French]
  • Cefalotinum
  • Cefalotinum [INN-Latin]
  • Cemastin
  • Cephalothin
  • Cephalothinum
  • Cephalotin
  • Coaxin
  • CT
  • EINECS 205-815-7
  • HSDB 3024
  • UNII-R72LW146E6

Systematic Names

  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-8-oxo-7-((2-thienylacetyl)amino)-, (6R,7R)-
  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-8-oxo-7-((2-thienylacetyl)amino)-, (6R-trans)-
  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(hydroxymethyl)-8-oxo-7-(2-(2-thienyl)acetamido)-, acetate (ester)
  • Cefalotin

Registry Numbers

CAS Registry Number

  • 153-61-7

FDA UNII

  • R72LW146E6

Other Registry Number

  • 2073-29-2

Related Registry Number

  • 58-71-9 (mono-hydrochloride salt)

System Generated Number

  • 0000153617

Structure Descriptors

InChI

1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1

InChIKey

XIURVHNZVLADCM-IUODEOHRSA-N

Smiles

CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)Cc3cccs3)SC1)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intracrebral 81mg/kg (81mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 863, 1965.
mouse LD50 intramuscular 7gm/kg (7000mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Byoin Yakugaku. Hospital Pharmacology. Vol. 3, Pg. 220, 1978.
mouse LD50 intravenous 4990mg/kg (4990mg/kg)   Chemotherapy Vol. 26(Suppl,
mouse LD50 subcutaneous > 4gm/kg (4000mg/kg)   Antimicrobial Agents and Chemotherapy. Vol. 3, Pg. 40, 1973.
rat LD50 intraperitoneal 4296mg/kg (4296mg/kg)   Antibiotiki. Vol. 26, Pg. 44, 1981.
rat LD50 intravenous > 5gm/kg (5000mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Chemotherapy Vol. 31(Suppl,
rat LD50 parenteral 23mg/kg (23mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 863, 1965.
rat LD50 subcutaneous 10gm/kg (10000mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES Chemotherapy Vol. 27(Suppl,

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 160-160.5 deg C   EXP
log P (octanol-water) 0.0 (none)   EXP
Water Solubility 158 mg/L 25 EST
Vapor Pressure 1.67E-14 mm Hg 25 EST
Henry's Law Constant 1.74E-17 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.40E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.